


The Reward of Humiliation

by HoneyNutFemios93



Series: The Swshies (formerly known as the Milo Fics) [1]
Category: Pocket Monsters | Pokemon (Main Video Game Series), Pocket Monsters | Pokemon - All Media Types, Pocket Monsters: Sword & Shield | Pokemon Sword & Shield Versions
Genre: Aftercare, Anal Fingering, Anal Fisting, Biting, Body Massage, Bottom Milo, Dubcon Cuddling, Dubcon Kissing, F/M, Femdom, Kissing, Laundry, Naked Male Clothed Female, Non-Consensual Kissing, dubcon, nipple sucking
Language: English
Status: Completed
Published: 2019-11-21
Updated: 2019-11-21
Packaged: 2021-02-25 20:31:53
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 1
Words: 2,521
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21513919
Author URL: https://archiveofourown.org/users/HoneyNutFemios93/pseuds/HoneyNutFemios93
Summary: Milo realizes he's in one of THOSE fan fictions. A late-night drabble about Pokemon Sword and Shield.
Relationships: Yarrow | Milo/Original Pokemon Trainer(s)
Series: The Swshies (formerly known as the Milo Fics) [1]
Series URL: https://archiveofourown.org/series/1556851
Comments: 1
Kudos: 7





	The Reward of Humiliation

**The Reward of Humiliation**

_-_-_

It wasn't often Milo hears back from people that challenged him in his Gym for months, let alone from someone that managed to beat the entire Galar League. So when he got a call from the new Galar League Champion, he was quick to answer. 

"Hello! This is Milo of Turffield, how may I help you?" Milo asked playing dumb. 

"Ah, yes. This is the Trainer that defeated you two weeks back. You available tomorrow evening?" the Trainer asked, her voice sounding awfully peculiar. 

It was wispy and soft, not one fitting of a champion calling someone that helped them on their first step to becoming a powerful trainer. He brushed this off as the poor girl already getting tired of her new position. 

"Yes of course! Where shall we meet?" Milo asked, now genuinely intrigued by this peculiar question. 

He didn't think that tomorrow evening he was meeting her in a fancy little motel in the middle of nowhere, in particular, wearing his stadium jersey after a good old fashioned bath. He liked being clean but he didn't understand why the Trainer did too at first. 

She showed up from her Flying Taxi as she was wearing her usual attire as well. Granted, that attire being a pretty pink dress with a grey wool jacket engulfing said dress and a nice green hat sitting on top of her head. She was cute, and nothing like the girl he saw earlier with a Scorbunny that trashed his entire team with fire in her eyes and cold blood through her icy cold veins. 

"Ready for me to treat myself?" she asked as she licked her lips. 

Milo towered the girl but he couldn't help but notice that she looked at her like an Obstagoon looks at a sweet innocent Wooloo. He didn't understand why she had such a strange look in her eye but he was ready to have their secret rendezvous in this motel regardless of what happens. 

As they walked to their room, Milo tried to make small talk. 

"So… How is championing the Galar Region?" he asked. 

"It's been rather boring. Now I have to fill up the Pokedex and it has been quite the chore," the Trainer replied as she rolled her eyes unimpressed by the question. 

"Oh… W-well I heard Grass-type Pokemon can be quite beautiful this time of year! Deerling from Unova are something I heard about on the regular! I never saw one in person though, but I bet taking care of one would be soooo cute!" Milo realized gushing about cute Pokemon might lift the Trainer's mood. Girls like cute Pokemon, right? 

The Trainer chuckled. Her mood seemed to have lifted. 

"You're too precious, Milo," the Trainer said as she held his hand into their room. 

There was a bathroom to their left and a queen-sized bed right in front of them. The motel also had a desk by the window and a TV by the foot of the bed. 

"Such a shame I have to corrupt you," the Trainer whispered almost ominously. Milo was baffled. 

"I don't follow," Milo said as he was trying to wrap his head around the comment. 

"Now… Sit down, and take off your scarf and hat," the Trainer purred.

Milo nodded. He figured it was rude to wear outerwear inside, so did so obediently. He then felt the Trainer slide next to him as he sat down on the bed. 

"Now… Do you want me to massage you?" the Trainer asked as she slid right next to him. 

Milo took time to think on the subject, "Actually, that sounds rather nice. I didn't think I'd need one usually but lately, I've been feeling stiff."

He tried to ignore the Trainer licking her lips as she blew softly into his ear. The Trainer was firm with her massage as she started by gently stroking his neck before his trapezius was groped a bit roughly. He could feel his back feeling much better but he also couldn't help but whimper when his body knew the Trainer was being rough on him. He yelped more loudly when he saw his pecs were cupped into the Trainer's small delicate hands. 

"I envy these breasts you have. A girl like me would die for them!" she said as she clenched these pecs tightly. 

"W-well they're not tits! This is just muscle, rather than fat!" Milo said crudely as his face began to turn red. When he thought he was getting goosebumps earlier from the tingling sensation of the Trainer's body massage, he can now feel himself glowing a feverish red. 

"Well, you seem embarrassed when I brought them up," the Trainer smiled a devilish grin as she said this. 

"P-please let go… I'll do anything!" Milo squeaked as he attempted to squeeze the girl's arms to a breaking point with his own more muscular ones. 

"Anything?" The Trainer raised a brow unphased by Milo's attempts at self-defense. 

Milo realized what he just said. 

"Lie down, and bare those tits for me," the Trainer said as she gently helped Milo lie down on a pillow. 

Milo did as he was told and bared his chest for her, lifting his jersey shirt up in the process.

"W-what did you want to do with me?" Milo asked as he was growing more afraid of the Trainer, more so than when he was down to his last Pokemon and her Scorbunny stared down at it hungrily. 

"Why to get another reward from you of course," the Trainer said. 

Before Milo could say another word she kissed him. He could hear himself squealing underneath her. He didn't know if he loved this or not. He managed to find an answer the minute the Trainer parted her lips away from his finally. 

"You are such a brat!" Milo whined as he can feel the Trainer begin to nibble him all over his neck and trapezius. 

"But I worked my way up for champion didn't I?" she asked before she bit around his left nipple. 

Milo muffled his own scream, which turned into a moan as her teeth let go and she began to suckle gently instead. 

She cooed him with an apology as she kissed all her nibble marks. Milo could feel himself tearing up again. 

He also tried to hide his own erection. Even though she was rough on him, he didn't know what she was going to do with him next. This probably made him more excited than he should. 

"Do you want me to play with you further?" the Trainer asked as she resumed her massaging, going back to lower on his back until eventually, he can feel her hands rub his round and toned posterior. 

"What do you have in mind?" Milo asked, now knowing a lot better that the Trainer is probably going to do something with his body. 

"Well, you've been hiding your magic Rapidash horn from me. My guess is you want me to be the one to penetrate you instead," the Trainer said as she observed him looking at her with an anxious glance. 

"P-penetrate? W-what do you mean?" Milo asked as he felt his voice crack from the shock that the Champion gave his body so much attention. 

He was aware she was talking about sex and that by 'magic Rapidash horn', she was referring to his penis. But he didn't think of any ways a girl could penetrate a man. That sounded a bit strange. 

"I'll show you, but only if you want me to," the Trainer said, though she sounded like she was starting to show remorse in her actions from earlier where she bit him. 

"Please… I insist," Milo said, still teary-eyed. He was genuinely curious as he wanted to know what she had in store for him. He arched his posterior closer to hers, as he thought maybe it might help her better. 

"You're such a good person. I am starting to feel bad I chose you for this," the Trainer said as she pulled out a glove that went over her arm.

It looked like she was preparing herself to carve out a Cramorant or an Unpheasant. Milo gulped. She then pulled out a Potion that would be used for Pokemon with her ungloved hand right out of her purse as she sprayed her gloved hand with it. 

With her ungloved hand, she gently tugged Milo's pants down before she began to gently rub around Milo's sphincter with a finger on her gloved hand. Milo squirmed as the Potion she used was cold. He could feel himself getting goosebumps. Then she pushed down on it. 

Milo began remembering his prostate exams and began to wince back at first, taking the Trainer's gloved finger with him as she merely laughed. She continued to push her finger further inside of him, up and down until she added another finger, and then another. Before long Milo realized her whole hand was inside of him, and then she clenched her hand. 

He realized he let out a soft bleat, the one a Wooloo or a Mareep make as he was feeling the Trainer's whole arm move inside of him. He didn't think this was how penetration worked, as no man's hard cock felt as bony, thick, and long like a small woman's arm going inside anyone, let alone a man as large as Milo was. 

"Are you okay? Do you want me to go back to just the fingers?" The Trainer asked as she was slowly pulling her arm out, though not pulling her hand out entirely. 

Milo shook his head but he meant to nod. He realized this mistake as she gently pushed her arm back in again. He could hear himself bleating again. He realized why and right away he was learning he was being fucked with, both figuratively AND literally. 

As she pulled again, she asked again. Not wanting to make the same mistake as before, Milo nodded and panted, "Yes! Please!" 

The Trainer had sighed as she finally pulled most of her hand out, but keeping two fingers inside. Milo could feel his anus, damaged as it was, feeling a bit of relief as the Trainer sprayed his whole posterior region with more of the Potion. If there was one thing he didn't know was that the Potion that was primarily meant for Pokemon also helped with humans as well. 

He could feel himself pushing his posterior toward the Trainer again. 

Milo wept gently as he was embarrassed from his bleating from whatever the Trainer was doing to him earlier. She tapped his prostate gently but that got Milo into now full-on crying like a Sobble. The Trainer kept gently rubbing there as Milo kept sobbing. He was like this because he was actually in pleasure. 

"Are you okay? Do you want me to stop?" The Trainer asked. 

Milo could feel he had some annoyance in that question. You idiot, this body massage should have been just a massage! Not whatever this nonsense is with the gloved hand cleaning him out and the bite marks on his left boob! He shook his head. 

Soon the gentle tapping from before became more frequent as soon Milo could feel himself about to cry out into orgasm. He tried to warn the Trainer as his head became hot from ecstasy. 

"T-Trainer! Wait! I… Ah! I'm… Ah! Ahh!!!" Milo climaxed as he felt his shorts soil with his semen. This whole time his two hands were covering his erection, but it seemed after the orgasm, he dropped his hands, revealing the tainted shorts. 

He noticed the Trainer undress his tired form as he was a sweaty mass of a dizzy, exhausted husk of his former self. He didn't even bother to ask, but he wished he didn't have to ruin his stadium uniform for her. 

"I'll take this down to the laundromat downstairs. I'll be back," the Trainer said giggling as if she was talking to a relative or a friend. 

Milo laid there for a bit, thinking about what just happened to him and if he could manage to tell the other Gym Leaders about this, which even included Raihan who blogged about almost anything in this equation. As he made his decision, the Trainer came back with an electric blanket.

“I thought you would get under the covers, Milo,” the Trainer said, half chuckling and half scolding Milo like a mother. 

“That really hurt,” Milo said with a frown. 

“Oh, really? I didn’t mean to hurt you, Milo. Just hear you cry just this once. That’s all,” the Trainer cooed as she helped tuck Milo into the bed, electric blanket over the comforter and sheets with the now naked Milo underneath all of it. The Trainer joined him under the covers, her body feeling nice spooning him. 

“Why me?” Milo asked as he was noticing the massaging from before coming back as his abdomen was being rubbed by her.

The Trainer took time to think on that question, still rubbing his stomach as Milo debated facing her or now.

“You’re Milo of Turffield… The first Gym Leader I had faced. You also looked pretty lonely by yourself. I figured the Turffield Gym Leader needed some attention,” she said as Milo finally turned to face her. She was now rubbing his rump, which would probably help as it hurt like Hell from the Trainer’s… penetration. 

“M-Me? Not really. I have gotten more challengers since you faced me,” Milo chuckled.

“But none of them were as deadly as me, right?” the Trainer asked as she tried to reach up and kiss him. Milo was a bit miffed by this exchange, but he figured that the awkward handshake they made after their first Pokemon battle was the longest one he had. Sometimes Milo wanted to imagine why it was so long. As they were kissing, Milo thought maybe the Trainer was projecting her own loneliness onto him and that was why he was a bit irritated by the comment. 

_-_-_

The next morning, Milo’s body was still aching from his night with the Trainer. He was happy the Trainer cleaned his stadium uniform but at the same time, he didn’t know what he could say about last night’s meeting. 

“Hey! Are you okay, Milo? You look out of it,” Nessa asked. 

“Me? Oh! Yeah… I’m just bummed out because… the Trainer challenged me to a rematch and despite everything, I lost! A real bummer, innit?” Milo chuckled. He didn’t want to tell Nessa what really happened.

“I guess so,” Nessa said, not really buying it as no one asks the first Gym Leader of the Galar region to a rematch. 

“Whelp! Water under the bridge you always say! That just means I have to train harder!” Milo guffawed feigning optimism.

“Good luck, mate,” Nessa rolled her eyes initially until she kept observing Milo walking awkwardly away, mumbling to himself about how the Trainer really was rough on him. Her eyes widened at first and then narrowed as a small grin was creeping on her face.


End file.
